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Polycrystal of pteridinone compounds or their salts and preparation method and application thereof

A compound and crystal form technology, applied in the field of medicine, can solve problems such as enlargement, and achieve the effects of good water solubility, high stability, and good crystallinity

Active Publication Date: 2019-05-31
SICHUAN KELUN BIOTECH BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to research, TLR7 agonists can stimulate and regulate the response of endogenous type I interferon (INF-ɑ / β), increase the downstream signaling interferon regulatory genes (ISGs), and exert immune antiviral effects, and have different effects on hepatitis B. genotype nonselective

Method used

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  • Polycrystal of pteridinone compounds or their salts and preparation method and application thereof
  • Polycrystal of pteridinone compounds or their salts and preparation method and application thereof
  • Polycrystal of pteridinone compounds or their salts and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1 4-amino-2-butoxy-8-((6-(4-methylpiperazin-1-yl)pyridin-3-yl)methyl)-7,8-dihydropteridine- Preparation of 6(5H)-ketone

[0077]

[0078] The first step: tert-butyl 4-(5-formylpyridin-2-yl)piperazine-1-carboxylate

[0079] The compound 6-bromonicotinaldehyde (1.0g, 5.376mmol), N-Boc-piperazine (1.0g, 5.376mmol) and DIEA (2.5mL) were added to 10mL of DME, heated to 120°C and stirred for 6.5 hours. Water was added, extracted with EA, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain 1.4 g of a yellow solid (yield 89.7%).

[0080] The second step: tert-butyl 4-(5-((ethoxycarbonylmethyl-amino)methyl)pyridin-2-yl)piperazine-1-carboxylate

[0081] Compound 4-(5-formylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (1.2g, 4.12mmol), glycine ethyl ester hydrochloride (1.2g, 8.60mmol) and cyanoboron Sodium hydride (0.6g, 9.548mmol) was added into 30mL methanol system, and the reaction was stirred at 20°C for 3 h...

Embodiment 2

[0097] The preparation of embodiment 2 crystal form I

[0098] Method 1: Weigh 0.1 g of the compound sample of formula I and disperse it in 5 ml of methanol, suspend and stir for 24 hours, filter and collect the crystals, dry in vacuum at 50°C for 1 hour to obtain a white powder, which is the crystal form I of the present invention, which 1 HNMR spectrum such as Figure 4 shown.

[0099] Structural characterization of Form I

[0100] X-ray powder diffraction (XRPD)

[0101] Adopt X`Pert3 Powder powder diffractometer to obtain the XRPD pattern of crystal form I, such as figure 1 As shown, the instrument is irradiated with Cu palladium and detected using Absolute scan at room temperature. The detection range is from 3.5° to 40°, the step size is 0.013, the dwell time is 50s, and the scan is performed once. The XRPD crystal form characterization data of Form I are shown in Table 1.

[0102] Table 1.

[0103]

[0104]

[0105]

[0106] Differential Scanning Calorim...

Embodiment 3

[0115] Embodiment 3 crystal form I stability test (stability investigation)

[0116] The crystal form I samples were placed in the following two groups of conditions respectively, and samples were taken from two batches before and after the first day and the thirty-first day to detect XRPD.

[0117] group

[0118] Test results: After being placed under the above conditions for 31 days and compared with the test results on the first day, it was found that the XRPD pattern was consistent and the crystal form did not change. It shows that the crystal form I has better stability.

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Abstract

The invention provides a polycrystal of pteridinone compounds or their salts, a method of preparing the polycrystal, a pharmaceutical composition containing the polycrystal, and application of the polycrystal in the preparation of drugs to treat TLR7-related diseases.

Description

technical field [0001] The present invention relates to the field of medicine, in particular, the present invention relates to polymorphs of tertidinone compounds or salts thereof, preparation methods and applications thereof. Background technique [0002] Viral hepatitis B is caused by the hepatitis B virus (HBV), and is an infectious disease characterized by inflammation of the liver. According to the report of the World Health Organization, about 2 billion people in the world have been infected with HBV, of which 350 million people are chronic HBV infected people, and about 1 million people die every year from liver failure, liver cirrhosis and primary hepatocellular carcinoma caused by HBV infection . [0003] Currently, the main means of prevention and treatment of viral hepatitis B are hepatitis B vaccine prevention, drug treatment such as interferon and nucleoside analogues. Administration of exogenous alpha-interferon (eg, recombinant alpha-interferon or pegylated ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D475/06A61K31/519A61P31/20
CPCY02A50/30
Inventor 王天明杨成喜蔡家强刘金明刘伟陈强强康熙伟王利春王晶翼
Owner SICHUAN KELUN BIOTECH BIOPHARMACEUTICAL CO LTD
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